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Ethanol → tert-butyl N-[4-[3-[2-(hydroxymethyl)-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2215981
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HRID 2215981 반응식
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]([C:10]1[S:11][C:12]([S:25][CH3:26])=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[CH3:28][C:29]1[C:34]2B(O)[O:36][CH2:37][C:33]=2[CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]([C:10]1[S:11][C:12]([S:25][CH3:26])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:34]3[C:33]([CH2:37][OH:36])=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:28])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

7

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HCID 702EthanolHCID 10340Sodium CarbonateHCID 218861847-Methyl-1,3-dihydro-2,1-benzoxaborol-1-olHCID 145857672tert-butyl N-[4-(3-bromophenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate2회

생성물 1

HCID 145857676tert-butyl N-[4-[3-[2-(hydroxymethyl)-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate
수율 40%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

The procedure used in Example 1: step c was followed using {[4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (Example 27 (50 mg, 0.1 mmol)), 7-methyl-3H-benzo[c][1,2]oxaborol-1-ol ((Example 5: step b) 59 mg, 0.4 mmol), Na2CO3 (2M, 0.8 mL, 1.6 mmol), Pd(PPh3)4 (29.4 mg, 0.025 mmol), ethanol (0.8 mL) and toluene (1.6 mL). Analogous aqueous workup and purification of the crude material by preparative TLC (40% EtOAc in hexanes) yielded the title compound (21 mg, 40%) as a light-yellow glass. 1H-NMR (CDCl3): δ 7.96 (m, 2H), 7.86 (m, 1H), 7.54 (m, 1H), 7.43 (m, 1H), 7.18–7.38 (m, 3H), 4.53 (d, 1H, J=13.3 Hz), 4.45 (d, 1H, J=13.3 Hz), 2.54 (s, 3H), 1.96 (s, 3H), 1.49 (s, 9H). ESI-MS (m/z): Calcd. for C25H28N2O5S3: 532.7; found: 532.9.

후처리

  1. customAnalogous aqueous workup and purification of the crude material by preparative TLC (40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-114853b659af44978bb2a46b7d73c36d
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07109354B2

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